N-(Benzylsulfonyl)-1-(3-cyano-5-oxo-6,7-dihydro-5H-pyrrolo-[3,4-b]pyridin-2-yl)piperidine-4-carboxamide

ID: ALA5286497

Max Phase: Preclinical

Molecular Formula: C21H21N5O4S

Molecular Weight: 439.50

Names and Identifiers

Canonical SMILES:  N#Cc1cc2c(nc1N1CCC(C(=O)NS(=O)(=O)Cc3ccccc3)CC1)CNC2=O

Standard InChI:  InChI=1S/C21H21N5O4S/c22-11-16-10-17-18(12-23-21(17)28)24-19(16)26-8-6-15(7-9-26)20(27)25-31(29,30)13-14-4-2-1-3-5-14/h1-5,10,15H,6-9,12-13H2,(H,23,28)(H,25,27)

Standard InChI Key:  JRKMDCOUGBAABY-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   39.3903  -12.7408    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   38.9813  -13.4439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.4414  -11.5135    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.1511  -11.1041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1483  -10.2814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4397   -9.8762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8572  -11.5108    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.8565  -12.3289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5608  -12.7363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   37.9770  -12.7402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9752  -13.5574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.6857  -12.3332    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.1011  -12.3363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.8079  -12.7465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   41.5073  -13.9732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.2169  -13.5661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.2161  -12.7447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.5095  -12.3383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7309  -11.1063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7375  -10.2850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9585  -10.0248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4703  -10.6854    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.9477  -11.3537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7123   -9.2456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
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  5  8  1  0
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  6 14  1  0
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  2 19  1  0
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 24 25  2  0
 25 20  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 26  1  0
 28 31  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5286497

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 439.50

Molecular Weight (Monoisotopic): 439.1314

AlogP: 1.06

#Rotatable Bonds: 5

Polar Surface Area: 132.26

Molecular Species: ACID

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.98

CX Basic pKa: 1.34

CX LogP: 0.85

CX LogD: -0.09

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.71

Np Likeness Score: -1.32

References

1. Kong D, Xue T, Guo B, Cheng J, Liu S, Wei J, Lu Z, Liu H, Gong G, Lan T, Hu W, Hu W, Yang Y..  (2019)  Optimization of P2Y₁₂ Antagonist Ethyl 6-(4-((Benzylsulfonyl)carbamoyl)piperidin-1-yl)-5-cyano-2-methylnicotinate (AZD1283) Led to the Discovery of an Oral Antiplatelet Agent with Improved Druglike Properties.,  62  (6.0): [PMID:30843696] [10.1021/acs.jmedchem.8b01971]

Source

Source(1):

• Scientific Literature